Propanedioyl dichloride → 1-(4-chlorophenyl)-1H-benzo[b][1,4]diazepine-2,4(3H,5H)-dione

HRID 1485373Notes

Reaction equation

HRID 1485373 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([NH2:15])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:4][CH:3]=1.[C:16](Cl)(=[O:21])[CH2:17][C:18](Cl)=[O:19]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:18](=[O:19])[CH2:17][C:16](=[O:21])[NH:15][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]2=3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 74269Propanedioyl dichlorideHCID 522323N-(4-chlorophenyl)benzene-1,2-diamine

Product 1

HCID 709793321-(4-chlorophenyl)-1H-benzo[b][1,4]diazepine-2,4(3H,5H)-dioneYield 60.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred refluxing solution of N1-(4-chlorophenyl)benzene-1,2-diamine (100.0 mg, 0.46 mmol) in toluene (20 mL) was added dropwise a solution of malonyl dichloride (65.00 mg, 0.46 mmol). After addition was completed, the reaction mixture was refluxed for 1 h. The solvent was removed in vacuo, the mixture was stirred with water (20 mL), extracted with DCM (10 mL*3), and then was purified by Prep-TLC (DCM:MeOH=30:1) to give 1-(4-chlorophenyl)-1H-benzo[b][1,4]diazepine-2,4(3H,5H)-dione (80.00 mg, 60%) as a white solid. LRMS (M+H+) m/z: calcd 286.05. found 286.

Workup

  1. additionAfter addition
  2. temperaturethe reaction mixture was refluxed for 1 h
  3. customThe solvent was removed in vacuo
  4. extractionextracted with DCM (10 mL*3)
  5. customwas purified by Prep-TLC (DCM:MeOH=30:1)

Sources & evidence

ORD record
ord-dbf004f27ee84c558045b28b69941f37
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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